View 15399 GILLIGAN COURT Winter Garden, FL MLS# O6365269
$699,000
4

Beds

3.1

Baths

2,758

Sq.Ft.

15399 GILLIGAN COURT

Winter Garden, FL

Courtesy of FCG REALTY
View 6152 MERIWETHER CRESCENT Winter Garden, FL MLS# O6365054
$814,900
5

Beds

3.1

Baths

3,367

Sq.Ft.

6152 MERIWETHER CRESCENT

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 14931 LEBEAU LOOP Winter Garden, FL MLS# O6364989
$849,000
4

Beds

3.1

Baths

2,832

Sq.Ft.

14931 LEBEAU LOOP

Winter Garden, FL

Courtesy of FLORIDA REALTY INVESTMENTS
The time to sell is now! THE TIME TO SELL IS NOW!
View 13374 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5105157
  • New Construction with Virtual Tour
1 of 28
$814,990
5

Beds

4.0

Baths

3,076

Sq.Ft.

13374 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6357 WILD PERSIMMON WAY Winter Garden, FL MLS# G5105172
$730,184
3

Beds

3.1

Baths

2,515

Sq.Ft.

6357 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 13848 PEACH ORCHARD WAY Winter Garden, FL MLS# O6365304
$800,000
5

Beds

4.0

Baths

3,598

Sq.Ft.

13848 PEACH ORCHARD WAY

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 13398 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5105139
  • New Construction with Virtual Tour
1 of 28
$723,990
4

Beds

2.1

Baths

2,235

Sq.Ft.

13398 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 13386 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5105140
  • New Construction with Virtual Tour
1 of 28
$819,990
5

Beds

4.0

Baths

3,065

Sq.Ft.

13386 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 13362 PEACEFUL MELODY DRIVE Winter Garden, FL MLS# G5105141
  • New Construction with Virtual Tour
1 of 28
$809,990
5

Beds

4.2

Baths

3,076

Sq.Ft.

13362 PEACEFUL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 8019 RAIL STREET Winter Garden, FL MLS# O6365660
$734,900
3

Beds

2.1

Baths

2,707

Sq.Ft.

8019 RAIL STREET

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 934 MCKINNON SQUARE Winter Garden, FL MLS# O6362523
$795,500
3

Beds

2.1

Baths

2,536

Sq.Ft.

934 MCKINNON SQUARE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 15607 SYLVESTER PALM DRIVE Winter Garden, FL MLS# O6364144
$739,000
3

Beds

2.0

Baths

2,092

Sq.Ft.

15607 SYLVESTER PALM DRIVE

Winter Garden, FL

Courtesy of THE C SMITH REAL ESTATE GROUP LLC
View 14494 BREAKWATER WAY Winter Garden, FL MLS# S5139023
$720,000
5

Beds

3.0

Baths

3,638

Sq.Ft.

14494 BREAKWATER WAY

Winter Garden, FL

Courtesy of NUMBER 1 BROKER, LLC
View 5526 NEW INDEPENDENCE PARKWAY Winter Garden, FL MLS# O6365476
$720,000
5

Beds

3.0

Baths

2,240

Sq.Ft.

5526 NEW INDEPENDENCE PARKWAY

Winter Garden, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 1016 HUNTSPOINT STREET Winter Garden, FL MLS# O6363691
$859,900
3

Beds

2.1

Baths

2,421

Sq.Ft.

1016 HUNTSPOINT STREET

Winter Garden, FL

Courtesy of LOKATION
View 6321 WILD PERSIMMON WAY Winter Garden, FL MLS# G5105005
$654,990
3

Beds

2.0

Baths

1,772

Sq.Ft.

6321 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6315 WILD PERSIMMON WAY Winter Garden, FL MLS# G5105013
$668,990
4

Beds

3.0

Baths

2,102

Sq.Ft.

6315 WILD PERSIMMON WAY

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 15309 HONEYBELL DRIVE Winter Garden, FL MLS# O6363784
$799,000
4

Beds

3.1

Baths

3,094

Sq.Ft.

15309 HONEYBELL DRIVE

Winter Garden, FL

Courtesy of COLDWELL BANKER REALTY
View 17330 LAKE STAR ROAD Winter Garden, FL MLS# O6362471
$839,000
4

Beds

3.0

Baths

2,795

Sq.Ft.

17330 LAKE STAR ROAD

Winter Garden, FL

Courtesy of TALENT REALTY SOLUTIONS
View 2022 TILLMAN AVE Winter Garden, FL MLS# O6363253
$680,000
4

Beds

4.0

Baths

2,981

Sq.Ft.

2022 TILLMAN AVE

Winter Garden, FL

Courtesy of LPT REALTY, LLC

About Winter Garden

The balance between reverence for yesterday and vibrant growth is reflected in the Winter Garden slogan, "A City with a Future…Preserving Its Past."  Walking down historic Plant Street or catching a glimpse of landmark buildings like Tanner Hall immediately creates an image of small-town life at its finest in the heart of this quaint Main Street community. At the same time, redevelopment and growth are evident at every turn.  Antique stores, ice cream shops, and charming cafés combine with dynamic new businesses and residential development.  Covering approximately 17 square miles, Winter Garden offers access to the West Orange Trail for biking or jogging in a naturally beautiful setting.  Other amenities include large parks, a public boat ramp on Lake Apopka, and recreational complexes for tennis, swimming, and sports play.  This vast area once covered by citrus groves is rapidly transforming into a suburban environment that preserves the friendly, intimate spirit of yesterday.  Residents enjoy easy access to Highway 50, the East West Expressway, and the Florida Turnpike.

Listings in Winter Garden, FL

774

Estimated median home price

$589,000
Winter Garden FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winter Garden, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winter Garden, FL.

Homes for Sale by Price in Winter Garden, FL

PriceCount
$0 - 100K6
$100K - 200K8
$200K - 300K64
$300K - 400K82
$400K - 500K132
$500K - 600K123
$600K - 700K85
$700K - 800K68
$800K - 900K63
$900K - 1M49
$1M - Max94

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family502
Townhouse117
Condo110
Commercial9
Rental224
Lots and Land32
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home1
Farms0

(Data as of 1/3/2026)

Information deemed reliable but not guaranteed.

Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

Data is updated as of 1/3/2026.